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Measuring a Successful Life: 6 Compassionate Questions to Ask Yourself

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Here's how to turn inward for your best answers to life's biggest questions...

"Am I OK?"

Most of us are constantly asking ourselves that question in our lives.

It might not always be conscious, but at some level we're holding ourselves up to a yardstick to see if we measure up.

I caught myself doing that just this morning. But this time, some wiser internal voice called bullshit on me.

Here's the story behind that moment of insight, how I came to it, and what it can teach all of us about how to really decide if we're happy with our lives or whether we need to move in a new direction.

(If you want to just skip straight to the six questions, though, you can do that by clicking here.)

Listen to Inner Wisdom, Not Self-Talk

Recently I set some goals for myself related to a reboot of my business and online presence. The experience of essentially losing my dad this Spring to rapid-onset dementia has left me with a new perspective on what matters most in life. And I want my work to reflect that more fully.

The timeline I set for making these changes was an ambitious one, and this morning I realized I had already fallen behind. My plan had relied on me getting a lot of writing accomplished over the holiday weekend. And while I got some good work done, it wasn't nearly as much as I had intended.

And so this morning the subtle self-criticism started. ("Well, Elaine. Could it be that you're motivated to do the planning but you don't have the self-discipline to do the actual work?")

Then the inner critic pulled out a big yardstick and held it up, comparing my feeble accomplishments to the visible successes of public figures I admire — people like Brené Brown, Scott Dinsmore, Tara Brach — Oprah Winfrey for God's sake.

But all of a sudden, a different internal voice spoke up. And with a loving sweep of her arm, she rejected that entire internal dialogue that had just been filling my head.

My friend and journaling partner, Anne, would call that the difference between listening to self-talk (e.g., ego, internalized shoulds, self-criticism) and listening to your inner wisdom.

The journaling I've been doing more regularly for the past 9 months — with Anne, at the Chrysalis Institute, and by myself — has been transformative. And a big part of that transformation is that the voice of my inner wisdom has become much louder and clearer.

Which I think is why I was able to hear her this morning over the noisy chattering of my negative self-talk.

Look to Internal Wisdom, Not External Standards

The message my wise self had for me was that the best answers about how I'm doing come from within myself, not from external sources or standards. And that I certainly shouldn't be using anyone else's life to measure my own.

It reminded me too that I am going through a grieving process related to my father. That professional goals aren't the only thing I'm working on right now. I'm doing important emotional work too, which takes time and much energy.

(A wise mentor once shared with me her observation that people do serious harm to themselves when they try to compare their insides with other people's outsides.)

It helps that I've been exposed lately to a couple of role models who are good at turning to their inner compasses for guidance and affirmation — or for a soulful kick-in-the-butt to themselves when they get off track...

My friend Katya is a great example of this. She left a stable career (by others' standards) in hospice social work to do what better aligns now with her soul's needs and her heart's longings: making art, and facilitating periodic retreats and workshops that promote healing, mindfulness, and spiritual deepening. She followed her heart in a geographic sense too — moving to Santa Fe where she knew almost no one at first. Currently her life is a little unsettled in some ways, but she continues the fierce inward listening, and that has brought her a peaceful sense that she is exactly where she needs to be.

Potter Kevin Crowe has just become a role model for me in this regard too. Several years ago, Bob and I bought one of his beautiful wood-fired bowls, and it has been a fixture in our kitchen ever since. So when we saw that a documentary had been made about him, we had to see it. We watched Out of the Fire last night, and while it was thrilling to see the almost miraculous process that brought our bowl into being, the thing that struck me the most about the film was Kevin's inspiring way of listening to his own inner guide (rather than societal messages) when it comes to questions of how to live his life and approach his art.

Katya and Kevin and my own wise inner voice reminded me this morning that true success is not about money, fame, or influence. Those things might be byproducts of success, but they aren't what really matters.

What matters is living a life of meaning and joy. What matters is making choices that feel true to your deepest beliefs and values, your most authentic self.

6 Questions to Ask Yourself

So as I wrote about all this in my journal this morning, here are the questions that surfaced. These are the things I'm now more consciously asking myself as I decide whether or not I'm on track.

I share them here in reverse order because it seems to me that each has its roots in the ones that follow...

#6: Am I following my own deepest passions?

Am I pursuing work that makes my heart sing, or is my career a reflection of what others think I should be doing? Am I spending my free time on activities that bring me more fully to life, or am I doing things out of a sense of obligation?

#5: Does my work contribute something of unique beauty and value to the world?

When it comes to my work, I must act like a good Girl Scout and ask myself: Have I left this place a little better than I found it? Because I want my life to mean something. That means not just making worthy contributions to the world, however, but also doing so in a way that only I could do.

#4: Does my way of being nourish others with whom I come in contact?

Do the people who interact with me — or even simply see my example — feel better as a result? Are they encouraged, affirmed, comforted, enlightened, or inspired? Are their lives just a little better because of my presence?

#3: Am I honoring my deepest self and what it needs from me?

Question #4 can't come at the expense of #3. I need to nourish myself too. In fact, I need to do it first. I need to listen well to my heart and to give it what it's asking of me. I need to be a caretaker of my whole self — body, mind, and spirit.

#2: Am I fully present and awake?

This is the foundation for all the other questions, really. Am I present with and awake to my heart? To the Sacred? To the miraculous details of each moment of this precious life? If I am, then answering the preceding questions becomes so much easier.

Using the Questions

(I'll get to Question #1 in a moment. Bear with me.)

The above questions all feel like more compassionate things to ask ourselves than the kinds of questions that are the default for many of us — ones like "Why didn't you...?" or "What's wrong with you?"

But it could still be easy to fall into the trap of using these questions as a measuring stick — and deciding that we've fallen short.

So let's not use them as "yes" or "no" questions that will signify our success or failure.

Instead, let's use them as intentions, as touchstones to help bring our focus back to what really matters.

But if you're struggling with that, try this instead...

Ditch the above questions and just ask yourself this last one:

#1: What must I do in order for my wisest self to feel I'm living up to my life's potential?

It's not a "yes" or "no". It's not a measuring stick.

It's a compass.

It's an invitation to look inward for your answers — not to your inner critic, but to the wise and compassionate version of yourself who will never lead you astray.

Let's Reject That Original Question...

In case you hadn't guessed: I'm a big believer in the power of good questions. But there's one question I want to reject, and it's the one I started with:

"Am I OK?"

Instead of confronting ourselves with critical questions, let's offer ourselves affirming answers.

For me, I've decided that the answer isn't "Yes, I am OK."

The answer is simply: "I am."

When I start from a place of "I am" — in the most holy sense of that statement — the rest of my answers all fall into place.


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